2009′s Worst Celebrity Halloween Costumes

Oh, man, celebrities and Halloween. The one day that they feel comfortable dressing even stupider than they usually do. In this feature, I’ll share some of the most douchebaggy of 2009’s celeb costumes, along with some trenchant commentary.

Jon Gosselin – Well, at least he’s not wearing any Ed Hardy that we can see. But seriously, dude, you’re already on the cover of every tabloid on Earth for being the biggest douchebag who ever lived – this is like me dressing as a guy with a computer who just happens to have six-pack abs.

Noah Cyrus – So this is Miley Cyrus’s younger sister. She’s nine years old. And apparently Billy Ray decided that it would be OK for her to dress as a witch who also maybe has sex with dudes for money. Seriously, girl – it’s not Whore-O-Ween. Whatever happened to dressing like a bumblebee or something?

Heidi Klum – Aw, baby. Usually I love your costumes, but this is just weird. It’s making me think about that episode of Mad Men where Roger Sterling does the Al Jolson thing. The only thing that would have made this work is if Seal dressed up like a dove.

Jessica Alba – Oh, come on. There’s a lot that you could do with a Dora the Explorer costume, especially since they sort of sexied up her character design earlier this year. That’s why Jessica’s costume is such an epic fail. This doesn’t say “Dora the Explorer” as much as it says “I went to American Apparel.”